WO2025086123A1

WO2025086123A1 - Anhydrous composition for caring for and/or making up keratin materials

Info

Publication number: WO2025086123A1
Application number: PCT/CN2023/126362
Authority: WO
Inventors: Chi Ma; Qirui TIAN; Xiaoming Wu; Qingsheng Tao
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 2023-10-25
Filing date: 2023-10-25
Publication date: 2025-05-01
Anticipated expiration: 2026-04-25
Also published as: FR3154609A3; FR3154609B3

Abstract

An anhydrous composition for caring for and/or making up keratin materials, comprises: (i) from 7 wt% to 20 wt% of ascorbic acid, relative to the total weight of the composition; (ii) polydatin; and (iii) at least one compound of formula (I) : wherein, R ₁ and R ₃ are different from or identical to each other, independently selected from hydrogen, C ₁-C ₂₀ acyl carbonyl, C ₂-C ₂₀ alkenyl carbonyl, C ₁-C ₂₀ alkyl, C ₂-C ₂₀ alkenyl and C ₂-C ₂₀ alkynyl; R ₂ is selected from C ₁-C ₂₀ alkyl, C ₂-C ₂₀ alkenyl and C ₂-C ₂₀ alkynyl.

Description

ANHYDROUS COMPOSITION FOR CARING FOR AND/OR MAKING UP KERATIN MATERIALS

TECHNICAL FIELD

The present invention relates to a cosmetic composition. In particular, the present invention relates to an anhyd rous composition for caring for and/or making up keratin materials. In addition, the present invention also relates to a non-therapeutic method for caring for and/or making up keratin materials.

BACKGROUND ART

The development of cosmetic products dedicated to caring for and/or making up the skin and/or lips, is permanent.

Different cosmetic prod ucts will com prise different cosmetic active ingredients due to the desired use.

The formation of free radicals is a widely accepted pivotal mechanism leading to skin aging. Antioxidants protect cells from the damage of oxidative stress by scavenging free radicals and inhibiting following oxidation reactions. The topical application of antioxidants is broadly used in skin care prod ucts to prevent skin aging.

Ascorbic acid is an antioxidant widely used in cosmetic products for anti-ageing. However, ascorbic acid is easy to form crystal in an anhyd rous system when its concentration is relatively high, rending the system com prising it not stable.

In addition, many products in markets are not effective in anti-aging since they can not cover all radical pathways for skin aging.

It is therefore desirable to provide stable compositions for caring for and/or making up of keratin materials, which can effectively combat with skin aging.

SUMMARY OF THE INVENTION

It is an object of the present invention to develop stable compositions caring for and/or making up of keratin materials, which can effectively combat with skin aging.

It is another object of the present invention to provide a non-therapeutic method for caring for and/or making up keratin materials with above compositions.

Accordingly, in a first aspect, the present invention relates to an anhydrous composition, preferably for caring for and/or making up keratin materials, comprising:

(i) from 7 wt. %to 20 wt. %of ascorbic acid, relative to the total weight of the composition;

(ii) polydatin; and

(iii) at least one compound of formula (I) :

wherein, R₁ and R₃ are different from or identical to each other, independently selected from hydrogen, C₁-C₂₀ acyl carbonyl, C₂-C₂₀ alkenyl carbonyl, C₁-C₂₀ alkyl, C₂-C₂₀ alkenyl and C₂-C₂₀ alkynyl; R₂ is selected from C₁-C₂₀ alkyl, C₂-C₂₀ alkenyl and C₂-C₂₀ alkynyl.

In a second aspect, the present invention relates to a non-therapeutic method for caring for and/or making u p keratin materials, comprising applying the composition according to the present invention to the keratin materials.

In a third aspect, the present invention relates to use of the composition according to the present invention for combating with skin aging.

Other characteristics and advantages of the invention will emerge more clearly on reading the description and the examples that follow.

DETAILED DESCRIPTION OF THE INVENTION

Un less otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art the present invention belongs to. When the definition of a term in the present description conflicts with the meaning as commonly understood by those skilled in the art the present invention belongs to, the definition described herein shall apply.

In that which follows and unless otherwise indicated, the limits of a range of values are included within this range, in particular in the expressions "between... and…" and "from... to... " .

Moreover, the expression "at least one" used in the present description is equivalent to the expression "one or more" .

The expression "and/or" used in the present description is equivalent to the expression "one or both" of indicated elements.

Throughout the instant application, the term “comprising” is to be interpreted as encompassing all specifically mentioned features as well optional, additional, unspecified ones. As used herein, the use of the term “comprising” also discloses the embodiment wherein no features other than the specifically mentioned features are present (i.e., “consisting of” ) .

Unless otherwise specified, all numerical values expressing amount of ingredients and the like which are used in the description and claims are to be understood as being modified by the term “about” . Accordingly, unless indicated to the contrary, the n umerical values and parameters described herein are approximate values which are capable of being changed according to the desired purpose as required.

For the purposes of the present invention, the term "anhydrous" means that the composition according to the present invention contains less than 5 wt. %and preferably less than 2 wt. %, more preferably less than 1 wt. %of water relative to the total weight of the composition, even more preferably, is free of water. Where appropriate, such small amounts of water may be provided by ingredients of the composition that contain it in residual amount, but are not deliberately provided.

As used herein, the term “keratin materials” refer to the skin and the lips. By “skin” , we intend to mean all the body skin, including the scalp. Preferably, the keratin material is the facial skin.

All percentages in the present invention refer to weight percentage, unless otherwise specified.

The composition according to the present invention comprises:

(i) from 7 wt. %to 20 wt. %of ascorbic acid, relative to the total weight of the anhydrous composition;

(ii) polydatin; and

(iii) at least one compound of formula (I) as defined above.

Ascorbic acid

According to the first aspect, the composition of the present invention comprises from 7 wt. %to 20 wt. %of ascorbic acid, relative to the total weight of the composition.

Ascorbic acid, also known as vitamin C, is in particular in the L form.

Ascorbic acid has the following structure:

As examples of commercial products of ascorbic acid, mention can be made of those sold by the company DSM Nutritional Products under the trade name Ascorbic Acid Fineby the company Northeast General Pharmaceutical Factory under the trade name Ascorbic Acid EP/BP/USP/FCC/or by the company CSPC Weishing Pharmaceutical under the name Ascorbic Acid 100

Advantageously, ascorbic acid is present in the com position of the present invention in an amount ranging from 9 wt. %to 18 %, preferably from 11 wt. %to 16 wt. %, more preferably from 12 wt. %to 14 wt. %, relative to the total weight of the com position.

Polydatin

According to the first aspect, the composition of the present invention comprises polydatin.

Polydatin is a polyphenol belonging to the chemical family of stilbenoids, which is also called piceid. Polydatin can be extracted from the root and rhizome of Polygonum cuspidatum and it can also be found in a variety of other sources, such as grape, peanut, hop cones, red wines, hop pel lets, cocoa-containing products, chocolate products and many daily diets.

Polydatin includes trans-polydatin and cis-polydatin. Trans-polydatin wil l isomerize into cis-polydatin.

Preferably, the polydatin is selected from trans-polydatin, cis-polydatin, and a combination thereof.

Trans-polydatin is 3, 4’, 5-trihydroxystibene-3-β-mono-D glucoside, a stilbenoid that is trans-resveratrol substituted at position 3 by a β-D-glucosyl residue, and hasthe following structure:

As examples of commercial products of polydatin, mention can be made of that sold under the name POLYGONUM CUSPIDATUM ROOT EXTRACT by the company GUILIN LAYN NATURAL INGREDIENTS.

Advantageously, the polydatin is present in the composition of the present invention in an amount ranging from 0.01 wt. %to 20 wt. %, preferably from 0.05 wt. %to 10 wt. %, more preferably from 0.1 wt. %to 5 wt. %, more preferably from 0.1 wt. %to 3 wt. %, relative to the total weight of the composition.

Compounds of formula (I)

According to the first aspect, the composition of the present invention comprises at least one at least one compound of formula (I) :

The compound of formula (I) is commercially available or can be synthesized by known method in the art.

Preferably, R₁ and R₃ are different from or identical to each other, independently selected from hyd rogen and C₁-C₁₀ alkyl.

Preferably, R₂ is a C₁-C₁₀ alkyl.

More preferably, R₁ and R₃ are different from or identical to each other, independently selected from hydrogen and C₁-C₄ alkyl.

More preferably, R₂ is a C₁-C₄ alkyl.

Most preferably, R₁ and R₃ are hydrogen.

Most preferably, R₂ is methyl or ethyl.

According to a preferred embodiment, R₁ and R₃ are independently selected from hydrogen, C₁-C₆ alkyl carbonyl, C₂-C₆ alkenyl carbonyl, C₁-C₆ alkyl, C₂-C₆ alkenyl group, C₃-C₆ alkynyl; R₂ is selected from C₁-C₆ alkyl, and C₂-C₆ alkenyl.

According to a further preferred embodiment, R₁ and R₃ are independently selected from hydrogen, linear or branched C₁-C₄ alkyl carbonyl, linear or branched C₂-C₄ alkenyl carbonyl, linear or branched C₁-C₄, linear or branched C₂-C₄ alkenyl group, linear or branched C₃-C₄ alkynyl group; R₂ is selected from linear or branched C₁-C₄ alkyl group, linear or branched C₂-C₄ alkenyl group.

According to a further preferred embodiment, R₁ and R₃ is hydrogen, R₂ is ethyl.

Most preferably, the compound of formula (I) is3-O-ethyl ascorbic acid.

3-O-ethyl ascorbic acid has the following structure:

As an example of commercial products of 3-O-ethyl ascorbic acid, mention can be made of that sold by the company CORUM under the trade name ET-VC (K) .

Advantageously, the compound of formula (I) is present in the composition of the present invention in an amount ranging from 0.1 wt. %to 10 %, preferably from 0.3 wt. %to 8 wt. %, more preferably from 0.5 wt. %to 5 wt. %, even more preferably from 0.5 wt. %to 3 wt. %, relative to the total weight of the composition.

Ferulic acid and/or derivatives thereof

Preferably, the composition of the present invention com prises at least one of ferulic acid and/or derivatives thereof.

Ferulic acid, CAS number of which is 1135-24-6, is also called4-Hydroxy-3-methoxycinnamic acid, which has the following formula:

Ferulic acid can be broadly found in giant fennel, the seeds of coffee, apple, artichoke, peanut, and orange, as well as in both seeds and cell walls of commelinid plants (such as rice, wheat, oats, and pineapple) . Like many natural phenols, it is a strong antioxidant that is very reactive toward free radicals and red uces oxidative stress. Many studies suggest that ferulic acid may have antitumor activity.

As derivatives of ferulic acid, mention can be made of salts and esters of ferulic acid, for example, sodium ferulate, feruloylaminoacid benzyl or methyl esters.

Preferably, the composition comprises at least one offerulic acid and sodium ferulate.

More preferably, the composition of the present invention comprises ferulic acid.

As an example of commerical product of ferulic acid, mention can be made of ORYZA FERULIX from ORYZA OIL&FAT CHEMICAL.

Advantageously, ferulic acid and/or derivative thereof is present in the composition of the present invention in an amount ranging from 0.01 wt. %to 20 wt. %, preferably from 0.1 wt. %to 15 wt. %, more preferably from 0.3 wt. %to 10 wt. %, more preferably from 0.5 wt. %to 3 wt. %, relative to the total weight of the composition.

Deep eutectic solvents

Advantageously, the composition of the present invention comprises one or more deep eutectic solvents for ascorbic acid.

As examples of deep eutectic solvents for ascorbic acid, mention can be made of amino acids and betaines.

Preferably, the composition of the present invention comprises one or more deep eutectic solvent for ascorbic acid selected from proline, sarcosine, alanine, betaine, and mixtures thereof.

Preferably, the composition of the present invention com prises betaine as deep eutectic solvents for ascorbic acid.

Advantageously, the deep eutectic solvent for ascorbic acid is present in the composition of the present invention in an amount ranging from 0.1 wt. %to 60 wt. %, preferably from 1 wt. %to 50 wt. %, more preferably from 3 wt. %to 30 wt. %, relative to the total weight of the composition.

Additional adjuvants or additives

The com position of the present invention may also contain conventional cosmetic adjuvants or additives, for instance fragrances, chelating agents, preserving agents and bactericides, surfactants, thickeners, pH regulators, and mixtures thereof.

The skilled person in the art can adjust the amount of the additional adjuvants or additives so as not to adversely impact the final use of the composition according to the present invention.

Hydrophilic phase

The com position of the present invention may comprise a hydrophilic phase.

Preferably, the hydrophilic phase comprises one or more organic solvents selected from monoalcohols having from 2 to 6 carbon atoms such as ethanol, isopropanol; polyols having from 2 to 20 carbon atoms, preferably from 2 to 10 carbon atoms, and preferentially having from 2 to 6 carbon atoms, such as glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol; glycol ethers (notably having from 3 to 16 carbon atoms) such as mono-, di-or tri-propylene glycol (C₁-C₄) alkyl ethers, mono-, di-or tri-ethylene glycol (C₁-C₄) alkyl ethers and mixtures thereof.

The term “polyol” here means an alcohol having two or more hydroxy groups.

The polyol may have a linear, branched or cyclic molecular structure.

Preferably, the hydrophilic phase comprises one or more C2-C6 polyols.

The C₂-C₆ polyol may be selected from glycerin, diglycerin, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, pentylene glycol, hexylene glycol, and a mixture thereof.

In the present invention, the definition of polyol includes all possible isomer. For example, propylene glycol includes 1, 3-propylene glycol, 1, 2-propylene glycol and 1, 1-propylene glycol. Butylene glycol includes 1, 4-butylene glycol, 1, 3-butylene glycol, 1, 2-butylene glycol, etc.

In a preferred embodiment, the hydrophilic phase comprises one or more C₂-C₆ polyol selected from propylene glycol, dipropylene glycol, butylene glycol, glycerin and a mixture thereof.

If presents, the hydrophilic phase is present in the composition of the present invention in an amount ranging from 40 wt. %to 92 wt. %, preferably from 70 wt. %to 90 wt. %, more preferably from 80 wt. %to 90 wt. %, relative to the total weight of the composition.

According to a particularly preferred embodiment, the present invention provides an anhydrous composition, preferably for caring for and/or making up keratin materials, comprising, relative to the total weight of the composition:

(i) from 11 wt. %to 16 wt. %of ascorbic acid;

(ii) from 0.5 wt. %to 3 wt. %of 3-O-ethyl ascorbic acid; and

(iii) from 0.1 wt. %to 3 wt. %of polydatin.

(i) from 11 wt. %to 16 wt. %of ascorbic acid;

(ii) from 0.5 wt. %to 3 wt. %of3-O-ethyl ascorbic acid;

(iii) from 0.1 wt. %to 3 wt. %of polydatin; and

(iv) from 0.5 wt. %to 3 wt. %of ferulic acid.

(i) from 11 wt. %to 16 wt. %of ascorbic acid;

(ii) from 0.5 wt. %to 3 wt. %of 3-O-ethyl ascorbic acid;

(iii) from 0.1 wt. %to 3 wt. %of polydatin;

(iv) from 0.5 wt. %to 3 wt. %of feru lic acid; and

(v) from 3 wt. %to 30 wt. %of betaine.

Method and use

The composition of the present invention can be used for caring for and/or making up keratin materials.

According to the second aspect, the present invention relates to a non-therapeutic method for caring for and/or making up keratin materials, comprising applying the composition according to the present invention to the keratin materials.

In particular, the keratin material can be the skin, for example the facial skin.

According to the third aspect, the present invention relates to use of the composition according to the present invention for combating with skin aging.

EXAMPLES

The examples that follow are given as non-limiting illustrations of the present invention.

Main raw materials used, trade names and supplier thereof are listed in Table 1.

Table 1

Invention Examples 1-3 and comparative examples 1-5

Compositions of invention examples (IE) 1-3 and comparative examples (CE) 1-5 were prepared based on the amounts of components given in Table 2. The amounts are given in%by weight relative to the total weight of the composition.

Table 2

Polygonum cuspidatum root extract*: containing 100 wt. %of polydatin.

Compositions of invention examples 1-3 represent compositions according to the present invention.

Compositions of comparative examples 1 and 2 do not comprise at least one compound of formula (I) .

Composition of comparative example 3 comprises more than 20 wt. %of ascorbic acid, relative to the total weight of the composition.

Composition of comparative example 4 does not comprise polydatin.

Composition of comparative example 5 does not comprise ascorbic acid.

Preparation process:

The com positions listed above were prepared by mixing all components with stirring and heating to 80℃ to obtain a transparent composition, then cooling down to room temperature.

Evaluation

Stability

The stability of each composition prepared was evaluated as follows.

Firstly, 5 samples of each composition to be evaluated were put in an oven with constant temperature of 25℃. After 24 hours, 4 samples were put in 4 tested ovens and another sample was taken out from the oven and put in the room temperature:

4 ovens: set to 4℃, 30℃, 37℃ and 45℃ respectively for 2 months.

If there is no macroscopic crystallization (appearance of crystals, grains, clusters) after a sample was stored for 2 months, then the stability of the sample will be evaluated as “Pass” .

If there is macroscopic crystallization (appearance of crystals, grains, clusters) after a sample was stored for 2 months, then the stability of the sample will be evaluated as “Fail” .

The results of the stability of compositions of invention examples 1-3 and comparative examples 1-5 were summarized below.

Table 3

It can be seen from Table 3 that the compositions of invention examples 1-3 are stable.

Anti-oxidation ability

The anti-oxidation ability of each composition was evalu ated by a SQUALENE TEST (thin layer) as follows:

a. preparing 1%squalene ethanol solution;

b. preparing squalene film on ground glass slides, with around 50 μg/cm²;

c. applying the composition on squalene film, with 9 repeat slides for one composition;

d. stressing "solar" irritation on each prepared slides (step c) for 5 J/cm² of UVA in total (calculated by irritation strength at 360nm) ;

e. extracting the oxidized squalene peroxides and squalene residue with methan ol on a lab shaker; and

f. quantifying the squalene peroxides and squalene extracted.

Results were summarized in Table 4

Table 4

NA: not tested since the composition tested is not stable.

Note: the less per-oxidized squalene, the better the anti-oxidation a bility is. When the per-oxidized squalene is less than 40%, the anti-oxidation a bility is deemed to be acceptable.

It can be seen that compositions of invention examples 1-3 have good anti-oxidation ability (i.e., anti-aging ability) and are stable.

Claims

An anhydrous composition, preferably for caring for and/or making up keratin materials, comprising:

(i) from 7 wt. %to 20 wt. %of ascorbic acid, relative to the total weight of the composition;

(ii) polydatin; and

(iii) at least one compound of formula (I) :

wherein, R₁ and R₃ are different from or identical to each other, independently selected from hydrogen, C₁-C₂₀ acyl carbonyl, C₂-C₂₀ alkenyl carbonyl, C₁-C₂₀ alkyl, C₂-C₂₀ alkenyl and C₂-C₂₀ alkynyl; R₂ is selected from C₁-C₂₀ alkyl, C₂-C₂₀ alkenyl and C₂-C₂₀ alkynyl.
Composition according to claim 1, wherein ascorbic acid is present in an amount ranging from 9 wt. %to 18%, preferably from 11 wt. %to 16 wt. %, more preferably from 12 wt. %to 14 wt. %, relative to the total weight of the composition.
Composition according to any of claims 1 or 2, wherein the polydatin is selected from trans-polydatin, cis-polydatin, and a combination thereof.
Composition according to any of claims 1 to 3, wherein the polydatin is present in the composition of the present invention in an amount ranging from 0.01 wt. %to 20 wt. %, preferably from 0.05 wt. %to 10 wt. %, more preferably from 0.1 wt. %to 5 wt. %, more preferably from 0.1 wt. %to 3 wt. %, relative to the total weight of the composition.
Composition according to any of claims 1 to 4, wherein in formula (I) ,

R₁ and R₃ are different from or identical to each other, independently selected from hydrogen and C₁-C₁₀ alkyl; R₂ is a C₁-C₁₀ alkyl,

preferably, R₁ and R₃ are different from or identical to each other, independently selected from hydrogen and C₁-C₄ alkyl; R₂ is a C₁-C₄ alkyl,

more preferably, R₁ and R₃ are hydrogen; R₂ is methyl or ethyl.
Composition according to any of claims 1 to 5, wherein the compound of formula (I) is present in an amount ranging from 0.1 wt. %to 10%, preferably from 0.3 wt. %to 8 wt. %, more preferably from 0.5 wt. %to 5 wt. %, even more preferably from 0.5 wt. %to 3 wt. %, relative to the total weight of the composition.
Composition according to any of claims 1 to 6, further comprising at least one of ferulic acid and/or derivatives thereof, the derivatives of ferulic acid are selected from salts, esters of ferulic acid and mixture thereof, preferably the composition comprises at least one of ferulic acid and sodium ferulate, more preferably, the composition comprises ferulic acid.
Composition according to claim 7, wherein ferulic acid and/or derivatives thereof is present in an amount ranging from 0.01 wt. %to 20 wt. %, preferably from 0.1 wt. %to 15 wt. %, more preferably from 0.3 wt. %to 10 wt. %, more preferably from 0.5 wt. %to 3 wt. %, relative to the total weight of the composition.
Composition according to any of claims 1 to 8, further comprising one or more deep eutectic solvents for ascorbic acid, preferably selected from amino acids, betaines and mixture thereof, more preferably selected from proline, sarcosine, alanine, betaine, and mixtures thereof, preferably the deep eutectic solvent for ascorbic acid is present in an amount ranging from 0.1 wt. %to 60 wt. %, preferably from 1 wt. %to 50 wt. %, more preferably from 3 wt. %to 30 wt. %, relative to the total weight of the composition.
Composition according to any of claims 1 to 9, further comprising a hydrophilic phase.
Composition according to claim 10, wherein the hydrophilic phase comprises one or more organic solvents selected from monoalcohols having from 2 to 6 carbon atoms; polyols having from 2 to 20 carbon atoms; glycol ethers having from 3 to 16 carbon atoms, and mixtures thereof, preferably selected from C2-C6 polyols, more preferably selected from propylene glycol, dipropylene glycol, butylene glycol, glycerin and a mixture thereof.
Composition according to claim 10 or 11, wherein the hydrophilic phase is present in an amount ranging from 40 wt. %to 92 wt. %, preferably from 70 wt. %to 90 wt. %, more preferably from 80 wt. %to 90 wt. %, relative to the total weight of the composition.
Composition according to claim 1, comprising, relative to the total weight of the composition:

(i) from 11 wt. %to 16 wt. %of ascorbic acid;

(ii) from 0.5 wt. %to 3 wt. %of 3-O-ethyl ascorbic acid;

(iii) from 0.1 wt. %to 3 wt. %of polydatin;

(iv) optionally, from 0.5 wt. %to 3 wt. %of ferulic acid; and

(v) optionally, from 3 wt. %to 30 wt. %of betaine.
A non-therapeutic method for caring for and/or making up keratin materials, comprising applying the composition according to any of claims 1 to 13 to the keratin materials.
Use of the composition according to any of claims 1 to 13 for combating with skin aging.